25 picks The 10 picks #1
Washington Irving's Sunnyside, Irvington, Hudson Valley Fridays–Sundays, Oct 2–31, 2026 (evening performances) Tickets from $40
Jonathan Kruk tells The Legend of Sleepy Hollow outdoors at Washington Irving's own home, with live music and a Horseman cameo — it sells out yearly
Storytelling Halloween Metro-North trip
#1 Fridays–Sundays, Oct 2–31, 2026 (evening performances) · Limited Run
Washington Irving's Sunnyside, Irvington, Hudson Valley Tickets from $40 Storytelling
Jonathan Kruk tells The Legend of Sleepy Hollow outdoors at Washington Irving's own home, with live music and a Horseman cameo — it sells out yearly
Add to calendar#2
Philipsburg Manor, Sleepy Hollow, Hudson Valley Bestbudbrian · CC BY-SA 3.0 · Wikimedia Commons Fridays–Sundays, Oct 2–31, 2026 (evenings) Adults $35
Fire performers, a roving brass band and the Headless Horseman in a sound-and-light show take over Philipsburg Manor — Sleepy Hollow at its spookiest
Halloween Sleepy Hollow Metro-North trip
#2 Fridays–Sundays, Oct 2–31, 2026 (evenings) · Limited Run
Philipsburg Manor, Sleepy Hollow, Hudson Valley Bestbudbrian · CC BY-SA 3.0 · Wikimedia Commons Adults $35 Halloween
Fire performers, a roving brass band and the Headless Horseman in a sound-and-light show take over Philipsburg Manor — Sleepy Hollow at its spookiest
Add to calendar#3
Van Cortlandt Manor, Croton-on-Hudson, Hudson Valley Sep 18–Nov 8, 2026 (select evenings; every night in October) Timed tickets from $24
More than 7,000 hand-carved jack o'lanterns light up an 18th-century manor, dinosaurs and a pumpkin carousel included — an easy train ride up
Halloween Hudson Valley Metro-North trip
#3 Sep 18–Nov 8, 2026 (select evenings; every night in October) · Limited Run
Van Cortlandt Manor, Croton-on-Hudson, Hudson Valley Timed tickets from $24 Halloween
More than 7,000 hand-carved jack o'lanterns light up an 18th-century manor, dinosaurs and a pumpkin carousel included — an easy train ride up
Add to calendar#4
Grounds For Sculpture, Hamilton, New Jersey Open daily; Fri-Sun to 9pm, Mon-Thu to 5pm $25 adults
Forty-two acres of accredited arboretum holding 300-plus contemporary sculptures, including Seward Johnson's uncanny life-size tableaux. It stays open to 9pm Friday and the evening ticket is $15.
Art Day trip
#4 Open daily; Fri-Sun to 9pm, Mon-Thu to 5pm · Limited Run
Grounds For Sculpture, Hamilton, New Jersey $25 adults Art
Forty-two acres of accredited arboretum holding 300-plus contemporary sculptures, including Seward Johnson's uncanny life-size tableaux. It stays open to 9pm Friday and the evening ticket is $15.
Add to calendar#5
Upright Citizens Brigade Theatre, East Village, Manhattan Through Oct 10 $25 in person
UCB's flagship improv show turns a guest monologist's true stories into 90 minutes of scenes — past guests include Tina Fey and Conan O'Brien.
Improv UCB Livestream option
#5 Through Oct 10 · Limited Run
Upright Citizens Brigade Theatre, East Village, Manhattan $25 in person Improv
UCB's flagship improv show turns a guest monologist's true stories into 90 minutes of scenes — past guests include Tina Fey and Conan O'Brien.
Add to calendar#6
Snug Harbor Cultural Center & Botanical Garden, Livingston / New Brighton, Staten Island Fri & Sat nights, Oct 2–31, 2026 $30
A flashlight ghost tour of Snug Harbor's darkest history — Chaplain Quinn's murder, Captain Randall's grave — with ghost-hunting gear in hand.
Ghost Tour Staten Island Halloween Season
#6 Fri & Sat nights, Oct 2–31, 2026 · Limited Run
Snug Harbor Cultural Center & Botanical Garden, Livingston / New Brighton, Staten Island $30 Ghost Tour
A flashlight ghost tour of Snug Harbor's darkest history — Chaplain Quinn's murder, Captain Randall's grave — with ghost-hunting gear in hand.
Add to calendar#7
Newtown Creek Nature Walk, Greenpoint, Brooklyn Alex Lozupone · CC BY 4.0 · Wikimedia Commons Oct 3–4 and Oct 10–11, 2026 — 2pm performances (VIP ritual 1pm) Ticket tiers from about $34
Headsets on, 40 guests follow dancers and giant puppets along Newtown Creek, recast as the River Styx, in an immersive Persephone myth.
Immersive Greenpoint Outdoors
#7 Oct 3–4 and Oct 10–11, 2026 — 2pm performances (VIP ritual 1pm) · One Weekend Only
Newtown Creek Nature Walk, Greenpoint, Brooklyn Alex Lozupone · CC BY 4.0 · Wikimedia Commons Ticket tiers from about $34 Immersive
Headsets on, 40 guests follow dancers and giant puppets along Newtown Creek, recast as the River Styx, in an immersive Persephone myth.
Add to calendar#8
Asylum NYC, Gramercy, Manhattan Through Oct 10 $25 general admission
The Neo-Futurists race a clock to perform 30 short plays in one hour at Asylum NYC, with a die roll deciding how many get rewritten.
30 Plays In 60 Minutes Late show Off-Off-Broadway
#8 Through Oct 10 · Limited Run
Asylum NYC, Gramercy, Manhattan $25 general admission 30 Plays In 60 Minutes
The Neo-Futurists race a clock to perform 30 short plays in one hour at Asylum NYC, with a die roll deciding how many get rewritten.
Add to calendar#9
Theaterlab, Garment District, Manhattan Sep 17–Oct 3, 2026 (limited run) $40 / $60 / $80 general admis…
Eight-time Obie winner David Greenspan plays A.E. Housman in a rare revival of Tom Stoppard's The Invention of Love — final performances now.
Final performances Stoppard revival Off-Off-Broadway
#9 Sep 17–Oct 3, 2026 (limited run) · Limited Run
Theaterlab, Garment District, Manhattan $40 / $60 / $80 general admis… Final performances
Eight-time Obie winner David Greenspan plays A.E. Housman in a rare revival of Tom Stoppard's The Invention of Love — final performances now.
Add to calendar#10
Circle Line, Pier 83, Hell's Kitchen, Manhattan Photograph by Mike Peel ( www.mikepeel.net ). · CC BY-SA 4.0 · Wikimedia Commons Sat, Oct 3, 2026; boarding 8pm, departs 8:30pm, returns midnight $30–$40 tiered advance tickets
Two decks, two DJs: one floor plays nothing but Depeche Mode, the other New Wave and 80s alternative, on a riverboat circling the harbor.
Boat party Depeche Mode 80s Dance
#10 Sat, Oct 3, 2026; boarding 8pm, departs 8:30pm, returns midnight · One Day Only
Circle Line, Pier 83, Hell's Kitchen, Manhattan Photograph by Mike Peel ( www.mikepeel.net ). · CC BY-SA 4.0 · Wikimedia Commons $30–$40 tiered advance tickets Boat party
Two decks, two DJs: one floor plays nothing but Depeche Mode, the other New Wave and 80s alternative, on a riverboat circling the harbor.
Add to calendarMore this weekend #11
Flushing Town Hall, Flushing, Queens Saturday · Oct 3, 2026 — 7pm dance lesson, 8pm performances $30 advance ($25 members)
Smyrneiko collective KELEPOÚRI meets Bronx Garifuna star Gogo Norales for the first time, with a dance lesson first, at Flushing Town Hall.
World music Dance Flushing
#11 Saturday · Oct 3, 2026 — 7pm dance lesson, 8pm performances · One Day Only
Flushing Town Hall, Flushing, Queens $30 advance ($25 members) World music
Smyrneiko collective KELEPOÚRI meets Bronx Garifuna star Gogo Norales for the first time, with a dance lesson first, at Flushing Town Hall.
Add to calendar#12
MCC Theater, Robert W. Wilson MCC Theater Space, Hell's Kitchen, Manhattan Sep 25 – Nov 1, 2026 (first previews; opens Oct 13) $40 for the first three perfo…
Anne Washburn's world premiere follows a Texas TikToker unravelling after a pride flag goes up across the street, starting previews at MCC.
First previews World premiere Anne Washburn
#12 Sep 25 – Nov 1, 2026 (first previews; opens Oct 13) · Limited Run
MCC Theater, Robert W. Wilson MCC Theater Space, Hell's Kitchen, Manhattan $40 for the first three perfo… First previews
Anne Washburn's world premiere follows a Texas TikToker unravelling after a pride flag goes up across the street, starting previews at MCC.
Add to calendar#13
Twisted Trails, Annadale, Staten Island Select nights Sep 26–Oct 31, 2026 $15–$25 per person by night
A haunted forest walk with 36 themed lands and four new giants on the trail — Staten Island's homegrown scare is in its sixth season.
Haunted trail Halloween Staten Island
#13 Select nights Sep 26–Oct 31, 2026 · Limited Run
Twisted Trails, Annadale, Staten Island $15–$25 per person by night Haunted trail
A haunted forest walk with 36 themed lands and four new giants on the trail — Staten Island's homegrown scare is in its sixth season.
Add to calendar#14
Snug Harbor Cultural Center & Botanical Garden, Livingston, Staten Island Saturday, October 3, 2026, 7–9 PM (doors 6:30 PM) General admission $20
FlamenKora weaves trumpet, flamenco guitar and Senegalese kora into African flamenco jazz in Snug Harbor's Carpenter's Shop.
Jazz World music
#14 Saturday, October 3, 2026, 7–9 PM (doors 6:30 PM) · One Day Only
Snug Harbor Cultural Center & Botanical Garden, Livingston, Staten Island General admission $20 Jazz
FlamenKora weaves trumpet, flamenco guitar and Senegalese kora into African flamenco jazz in Snug Harbor's Carpenter's Shop.
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Send me this weekend's list #15
Upright Citizens Brigade Theatre, East Village, Manhattan Nightscream · CC BY 3.0 · Wikimedia Commons Saturday · Oct 3, 2026, 7pm $20 plus fees in person
A monthly UCB variety hour of Black comedians doing improv, sketch and stand-up — the show The New York Times called the city's funniest.
Variety Black comedians UCB
#15 Saturday · Oct 3, 2026, 7pm · One Day Only
Upright Citizens Brigade Theatre, East Village, Manhattan Nightscream · CC BY 3.0 · Wikimedia Commons $20 plus fees in person Variety
A monthly UCB variety hour of Black comedians doing improv, sketch and stand-up — the show The New York Times called the city's funniest.
Add to calendar#16
La MaMa — The Downstairs, East Village, Manhattan Oct 1–4, 2026 (Queer New York Festival runs Oct 1–11, 2026) $30 adults
Argentine actress Maiamar Abrodos turns a stage-design class into her life story as a trans woman — opening La MaMa's Queer New York Festival.
Theater East Village Queer
#16 Oct 1–4, 2026 (Queer New York Festival runs Oct 1–11, 2026) · One Weekend Only
La MaMa — The Downstairs, East Village, Manhattan $30 adults Theater
Argentine actress Maiamar Abrodos turns a stage-design class into her life story as a trans woman — opening La MaMa's Queer New York Festival.
Add to calendar#17
WP Theater, Upper West Side, Manhattan Sep 26 – Oct 25, 2026 Choose Your Price: $20 (limit…
A London teen sets a twisted online trap to find her missing brother in Melis Aker's darkly funny world premiere at WP Theater.
World premiere Starts this weekend Dark comedy
#17 Sep 26 – Oct 25, 2026 · Limited Run
WP Theater, Upper West Side, Manhattan Choose Your Price: $20 (limit… World premiere
A London teen sets a twisted online trap to find her missing brother in Melis Aker's darkly funny world premiere at WP Theater.
Add to calendar#18
Caveat, Lower East Side, Manhattan Saturday · Oct 3, 2026, 7pm (doors 6:30pm) $15 advance
YouTube tour guide and comic Tom Delgado mixes NYC history, trivia with prizes and comedian friends, with author David Conrad-Perez as guest.
NYC history Trivia Stand-up
#18 Saturday · Oct 3, 2026, 7pm (doors 6:30pm) · One Day Only
Caveat, Lower East Side, Manhattan $15 advance NYC history
YouTube tour guide and comic Tom Delgado mixes NYC history, trivia with prizes and comedian friends, with author David Conrad-Perez as guest.
Add to calendar#19
Union Hall, Park Slope, Brooklyn Saturday · Oct 3, 2026, 10pm (doors 9:30pm) $25.69
Comedian Hoodo Hersi headlines her show Extraordinary Alien in Union Hall's basement stage — a late-night Park Slope set.
Stand-up Late show Basement room
#19 Saturday · Oct 3, 2026, 10pm (doors 9:30pm) · One Day Only
Union Hall, Park Slope, Brooklyn $25.69 Stand-up
Comedian Hoodo Hersi headlines her show Extraordinary Alien in Union Hall's basement stage — a late-night Park Slope set.
Add to calendar#20
Rockaway Theatre Company, The John Gilleece Theater at Fort Tilden, Rockaway Park (the Rockaways), Queens Sep 25–Oct 11, 2026 — 8pm Sep 25–26, Oct 1–3 and Oct 9–10; 2pm Sep 27, Oct 4 and Oct 11 Adults $20
Wilde's cucumber sandwiches and mistaken identities come to a converted Fort Tilden army building by the beach, staged by the Rockaways' own troupe.
Theater Rockaways Community
#20 Sep 25–Oct 11, 2026 — 8pm Sep 25–26, Oct 1–3 and Oct 9–10; 2pm Sep 27, Oct 4 and Oct 11 · Limited Run
Rockaway Theatre Company, The John Gilleece Theater at Fort Tilden, Rockaway Park (the Rockaways), Queens Adults $20 Theater
Wilde's cucumber sandwiches and mistaken identities come to a converted Fort Tilden army building by the beach, staged by the Rockaways' own troupe.
Add to calendar#21
Theatre Row (Mint Theater Company), Theatre Row, Manhattan Oct 3–Nov 7, 2026 CheapTix from $27.50
Mint Theater revives Cicely Hamilton's 1911 governess drama Phyl, once blocked from an Oxford premiere, with Stereophonic's Lily Ganser.
First performances Rediscovered play Off-Broadway
#21 Oct 3–Nov 7, 2026 · Limited Run
Theatre Row (Mint Theater Company), Theatre Row, Manhattan CheapTix from $27.50 First performances
Mint Theater revives Cicely Hamilton's 1911 governess drama Phyl, once blocked from an Oxford premiere, with Stereophonic's Lily Ganser.
Add to calendar#22
Elsewhere (Zone One), Bushwick, Brooklyn Saturday · Oct 3, 2026, 7pm (16+) $20 plus fees
Bedroom-pop and alt-R&B songwriter Tim Atlas plays Elsewhere's intimate Zone One stage in Bushwick, sharing an early bill with Harrison Lipton.
Indie R&B Bushwick Early show
#22 Saturday · Oct 3, 2026, 7pm (16+) · One Day Only
Elsewhere (Zone One), Bushwick, Brooklyn $20 plus fees Indie R&B
Bedroom-pop and alt-R&B songwriter Tim Atlas plays Elsewhere's intimate Zone One stage in Bushwick, sharing an early bill with Harrison Lipton.
Add to calendar#23
Theater for the New City, East Village, Manhattan Sep 17–Oct 4, 2026 — Thu–Sat 8pm, Sun 3pm $20
Eleven musicians with portable electric guitars and percussion play while moving through choreographed formations in Patrick Grant's piece.
Music theater East Village Closing weekend
#23 Sep 17–Oct 4, 2026 — Thu–Sat 8pm, Sun 3pm · Limited Run
Theater for the New City, East Village, Manhattan $20 Music theater
Eleven musicians with portable electric guitars and percussion play while moving through choreographed formations in Patrick Grant's piece.
Add to calendar#24
Theater for the New City, East Village, Manhattan Sep 17–Oct 4, 2026 — Thu–Sat 8pm, Sun 3pm $20
A Times obituary writer interviews the college president who ruined her life in Rebecca Chace's revenge thriller, closing on First Avenue.
Theater East Village Closing weekend
#24 Sep 17–Oct 4, 2026 — Thu–Sat 8pm, Sun 3pm · Limited Run
Theater for the New City, East Village, Manhattan $20 Theater
A Times obituary writer interviews the college president who ruined her life in Rebecca Chace's revenge thriller, closing on First Avenue.
Add to calendarAccessories - a play by Ian Gould